JP6473518B2 - アリール又はヘテロアリール置換の５−ヒドロキシ−１，７−ナフチリジン化合物、その製造方法及び医薬の使用 - Google Patents
アリール又はヘテロアリール置換の５−ヒドロキシ−１，７−ナフチリジン化合物、その製造方法及び医薬の使用 Download PDFInfo
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- JP6473518B2 JP6473518B2 JP2017551702A JP2017551702A JP6473518B2 JP 6473518 B2 JP6473518 B2 JP 6473518B2 JP 2017551702 A JP2017551702 A JP 2017551702A JP 2017551702 A JP2017551702 A JP 2017551702A JP 6473518 B2 JP6473518 B2 JP 6473518B2
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- methyl ester
- acid methyl
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- hydroxy
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- -1 5-hydroxy-1,7-naphthyridine compound Chemical class 0.000 title claims description 53
- 238000000034 method Methods 0.000 title claims description 20
- 239000003814 drug Substances 0.000 title claims description 14
- 230000008569 process Effects 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 261
- 238000006243 chemical reaction Methods 0.000 claims description 200
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 90
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 75
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 73
- 150000001875 compounds Chemical class 0.000 claims description 72
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 69
- 238000010992 reflux Methods 0.000 claims description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 50
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 48
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 47
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 44
- 239000008096 xylene Substances 0.000 claims description 44
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical group BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 39
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 claims description 37
- 108090000394 Erythropoietin Proteins 0.000 claims description 35
- 102000003951 Erythropoietin Human genes 0.000 claims description 35
- 229940105423 erythropoietin Drugs 0.000 claims description 35
- 238000004519 manufacturing process Methods 0.000 claims description 33
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 31
- 239000000126 substance Substances 0.000 claims description 27
- 239000004471 Glycine Substances 0.000 claims description 24
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 claims description 24
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 24
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 23
- 239000005695 Ammonium acetate Substances 0.000 claims description 23
- 235000019257 ammonium acetate Nutrition 0.000 claims description 23
- 229940043376 ammonium acetate Drugs 0.000 claims description 23
- 229950005499 carbon tetrachloride Drugs 0.000 claims description 22
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 22
- 150000004702 methyl esters Chemical class 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 229910052742 iron Inorganic materials 0.000 claims description 16
- 230000001737 promoting effect Effects 0.000 claims description 16
- 206010021143 Hypoxia Diseases 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 208000007502 anemia Diseases 0.000 claims description 12
- 102000004079 Prolyl Hydroxylases Human genes 0.000 claims description 11
- 108010043005 Prolyl Hydroxylases Proteins 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- 239000007810 chemical reaction solvent Substances 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 8
- 208000017667 Chronic Disease Diseases 0.000 claims description 7
- 238000005893 bromination reaction Methods 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 230000002757 inflammatory effect Effects 0.000 claims description 7
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 6
- 102000004127 Cytokines Human genes 0.000 claims description 6
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical group Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 claims description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 230000031709 bromination Effects 0.000 claims description 5
- ZGXJTSGNIOSYLO-UHFFFAOYSA-N 88755TAZ87 Chemical compound NCC(=O)CCC(O)=O ZGXJTSGNIOSYLO-UHFFFAOYSA-N 0.000 claims description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical group [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 4
- 108010075016 Ceruloplasmin Proteins 0.000 claims description 4
- 102100023321 Ceruloplasmin Human genes 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 102000014150 Interferons Human genes 0.000 claims description 4
- 108010050904 Interferons Proteins 0.000 claims description 4
- 102000015696 Interleukins Human genes 0.000 claims description 4
- 108010063738 Interleukins Proteins 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 102000004338 Transferrin Human genes 0.000 claims description 4
- 108090000901 Transferrin Proteins 0.000 claims description 4
- 108010033576 Transferrin Receptors Proteins 0.000 claims description 4
- 102000007238 Transferrin Receptors Human genes 0.000 claims description 4
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 4
- 239000001099 ammonium carbonate Substances 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 150000001555 benzenes Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 claims description 4
- 210000003958 hematopoietic stem cell Anatomy 0.000 claims description 4
- 229940079322 interferon Drugs 0.000 claims description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
- 230000004044 response Effects 0.000 claims description 4
- 201000003068 rheumatic fever Diseases 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 4
- 230000000087 stabilizing effect Effects 0.000 claims description 4
- 239000012581 transferrin Substances 0.000 claims description 4
- 102000003390 tumor necrosis factor Human genes 0.000 claims description 4
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- 229910004664 Cerium(III) chloride Inorganic materials 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 3
- 229940043215 aminolevulinate Drugs 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 210000003924 normoblast Anatomy 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- MENYRYNFSIBDQN-UHFFFAOYSA-N 5,5-dibromoimidazolidine-2,4-dione Chemical compound BrC1(Br)NC(=O)NC1=O MENYRYNFSIBDQN-UHFFFAOYSA-N 0.000 claims description 2
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 claims description 2
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 2
- PNQUMVYVIMOUHE-UHFFFAOYSA-N COC=O.Oc1cncc2ncccc12 Chemical compound COC=O.Oc1cncc2ncccc12 PNQUMVYVIMOUHE-UHFFFAOYSA-N 0.000 claims description 2
- 229910021590 Copper(II) bromide Inorganic materials 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- 235000012538 ammonium bicarbonate Nutrition 0.000 claims description 2
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 2
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- 238000005815 base catalysis Methods 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 102100031939 Erythropoietin Human genes 0.000 claims 2
- 208000030760 Anaemia of chronic disease Diseases 0.000 claims 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims 1
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- 238000004440 column chromatography Methods 0.000 description 83
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 82
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- KPZSTOVTJYRDIO-UHFFFAOYSA-K trichlorocerium;heptahydrate Chemical compound O.O.O.O.O.O.O.Cl[Ce](Cl)Cl KPZSTOVTJYRDIO-UHFFFAOYSA-K 0.000 description 20
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- FHVWOVNXJQTAHQ-UHFFFAOYSA-N methyl 2-(bromomethyl)-6-(3-chlorophenyl)pyridine-3-carboxylate Chemical compound COC(C1=C(N=C(C=C1)C1=CC(=CC=C1)Cl)CBr)=O FHVWOVNXJQTAHQ-UHFFFAOYSA-N 0.000 description 2
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- YZWQCCUQUWXMRQ-UHFFFAOYSA-N methyl 2-(bromomethyl)-6-(4-bromophenyl)pyridine-3-carboxylate Chemical compound COC(C1=C(N=C(C=C1)C1=CC=C(C=C1)Br)CBr)=O YZWQCCUQUWXMRQ-UHFFFAOYSA-N 0.000 description 2
- BODGZIOOFCUNHV-UHFFFAOYSA-N methyl 2-(bromomethyl)-6-(4-tert-butylphenyl)pyridine-3-carboxylate Chemical compound COC(C1=C(N=C(C=C1)C1=CC=C(C=C1)C(C)(C)C)CBr)=O BODGZIOOFCUNHV-UHFFFAOYSA-N 0.000 description 2
- LSOUTHSFOVYTOG-UHFFFAOYSA-N methyl 2-(bromomethyl)-6-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylate Chemical compound N1=C(CBr)C(C(=O)OC)=CC=C1C1=CC=C(C(F)(F)F)C=C1 LSOUTHSFOVYTOG-UHFFFAOYSA-N 0.000 description 2
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- MAVYDHQSHVQVAG-UHFFFAOYSA-N methyl 2-[1-[(2-methoxy-2-oxoethyl)-(4-methylphenyl)sulfonylamino]ethyl]-6-(3-nitrophenyl)pyridine-3-carboxylate Chemical compound COC(C1=C(N=C(C=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(C)N(S(=O)(=O)C1=CC=C(C=C1)C)CC(=O)OC)=O MAVYDHQSHVQVAG-UHFFFAOYSA-N 0.000 description 2
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- RPNXFONDMPGFFD-UHFFFAOYSA-N methyl 2-[[(2-methoxy-2-oxoethyl)-(4-methylphenyl)sulfonylamino]methyl]-6-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylate Chemical compound COC(C1=C(N=C(C=C1)C1=CC=C(C=C1)C(F)(F)F)CN(S(=O)(=O)C1=CC=C(C=C1)C)CC(=O)OC)=O RPNXFONDMPGFFD-UHFFFAOYSA-N 0.000 description 2
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- AGIGCBFINWOSNG-UHFFFAOYSA-N methyl 6-(3-bromophenyl)-2-[1-[(2-methoxy-2-oxoethyl)-(4-methylphenyl)sulfonylamino]ethyl]pyridine-3-carboxylate Chemical compound COC(C1=C(N=C(C=C1)C1=CC(=CC=C1)Br)C(C)N(S(=O)(=O)C1=CC=C(C=C1)C)CC(=O)OC)=O AGIGCBFINWOSNG-UHFFFAOYSA-N 0.000 description 2
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- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 102100035070 von Hippel-Lindau disease tumor suppressor Human genes 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510141555.2 | 2015-03-27 | ||
| CN201510141555.2A CN106146491B (zh) | 2015-03-27 | 2015-03-27 | 被芳基或杂芳基取代的5‑羟基‑1,7‑萘啶化合物、其制备方法及其制药用途 |
| PCT/CN2015/097245 WO2016155358A1 (fr) | 2015-03-27 | 2015-12-14 | Composé de 5-hydroxy-1,7-naphtyridine substitué par aryle ou hétéroaryle, son procédé de préparation et son utilisation pharmaceutique |
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| Publication Number | Publication Date |
|---|---|
| JP2018510200A JP2018510200A (ja) | 2018-04-12 |
| JP6473518B2 true JP6473518B2 (ja) | 2019-02-20 |
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| JP2017551702A Active JP6473518B2 (ja) | 2015-03-27 | 2015-12-14 | アリール又はヘテロアリール置換の５−ヒドロキシ−１，７−ナフチリジン化合物、その製造方法及び医薬の使用 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9994566B2 (fr) |
| EP (1) | EP3287456B1 (fr) |
| JP (1) | JP6473518B2 (fr) |
| CN (1) | CN106146491B (fr) |
| WO (1) | WO2016155358A1 (fr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107522606B (zh) * | 2017-10-11 | 2020-04-14 | 南京工业大学 | 2-甲基-4-羰基-2,4-二苯基丁醛的合成方法 |
| CN108383763B (zh) * | 2018-04-26 | 2019-12-03 | 湖南文理学院 | 一种β-羰基砜类化合物的合成方法 |
| US11713298B2 (en) * | 2018-05-09 | 2023-08-01 | Akebia Therapeutics, Inc. | Process for preparing 2-[[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino]acetic acid |
| CN110878096A (zh) * | 2018-09-05 | 2020-03-13 | 石药集团中奇制药技术（石家庄）有限公司 | 一种1,7-萘啶类衍生物及其制备方法和用途 |
| CA3235718A1 (fr) | 2021-10-28 | 2023-05-04 | Insilico Medicine Ip Limited | Inhibiteurs de la proteine contenant un domaine prolyl hydroxylase (phd) et leurs utilisations |
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| AR037517A1 (es) * | 2001-11-05 | 2004-11-17 | Novartis Ag | Derivados de naftiridinas, un proceso para su preparacion, composicion farmaceutica y el uso de los mismos para la preparacion de un medicamento para el tratamiento de una enfermedad inflamatoria |
| CN102977015B (zh) * | 2003-06-06 | 2015-05-06 | 菲布罗根有限公司 | 含氮杂芳基化合物及其在增加内源性促红细胞生成素中的用途 |
| JP2007191451A (ja) * | 2006-01-20 | 2007-08-02 | Tokai Univ | プロリル水酸化酵素阻害剤 |
| GB0601951D0 (en) * | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| TW200808793A (en) * | 2006-03-07 | 2008-02-16 | Smithkline Beecham Corp | Prolyl hydroxylase inhibitors |
| US20100056563A1 (en) * | 2007-04-18 | 2010-03-04 | Deodialsingh Guiadeen | Novel 1.8-naphthyridine compounds |
| AU2008319229A1 (en) * | 2007-11-02 | 2009-05-07 | Fibrogen, Inc. | Methods for reducing blood pressure |
| WO2012106472A1 (fr) * | 2011-02-02 | 2012-08-09 | Fibrogen, Inc. | Dérivés de naphthyridine en tant qu'inhibiteurs d'un facteur inductible par l'hypoxie |
-
2015
- 2015-03-27 CN CN201510141555.2A patent/CN106146491B/zh active Active
- 2015-12-14 US US15/561,464 patent/US9994566B2/en active Active
- 2015-12-14 EP EP15887309.1A patent/EP3287456B1/fr active Active
- 2015-12-14 JP JP2017551702A patent/JP6473518B2/ja active Active
- 2015-12-14 WO PCT/CN2015/097245 patent/WO2016155358A1/fr active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| EP3287456A4 (fr) | 2018-10-03 |
| US20180118738A1 (en) | 2018-05-03 |
| US9994566B2 (en) | 2018-06-12 |
| WO2016155358A1 (fr) | 2016-10-06 |
| EP3287456B1 (fr) | 2020-08-26 |
| CN106146491A (zh) | 2016-11-23 |
| EP3287456A1 (fr) | 2018-02-28 |
| JP2018510200A (ja) | 2018-04-12 |
| CN106146491B (zh) | 2017-12-12 |
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